2879-16-5

Basic information

• Product Name: 3,7-Dihydro-8-(hydroxymethyl)-1,3-dimethyl-1H-purine-2,6-dione
• Synonyms: 3,7-Dihydro-8-(hydroxymethyl)-1,3-dimethyl-1H-purine-2,6-dione;8-(Hydroxymethyl)theophyline;8-(hydroxymethyl)-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione;8-(hydroxymethyl)-1,3-dimethyl-3,7-dihydro-1H-purine-2,6-dione
• CAS NO: 2879-16-5
• Molecular Formula: C₈H₁₀N₄O₃
• Molecular Weight: 210.19
• Mol File: 2879-16-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 248 °C
• Boiling Point: 531.1°C at 760 mmHg
• Flash Point: 275°C
• Appearance: /
• Density: 1.537g/cm³
• Vapor Pressure: 4.16E-12mmHg at 25°C
• Refractive Index: 1.645
• PKA: 8.01±0.70(Predicted)
• CAS DataBase Reference: 3,7-Dihydro-8-(hydroxymethyl)-1,3-dimethyl-1H-purine-2,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,7-Dihydro-8-(hydroxymethyl)-1,3-dimethyl-1H-purine-2,6-dione(2879-16-5)
• EPA Substance Registry System: 3,7-Dihydro-8-(hydroxymethyl)-1,3-dimethyl-1H-purine-2,6-dione(2879-16-5)

Safety Data

• Hazardous Substances Data: 2879-16-5(Hazardous Substances Data)

Usage

General Description

3,7-Dihydro-8-(hydroxymethyl)-1,3-dimethyl-1H-purine-2,6-dione, also known as theophylline, is a chemical compound that belongs to the xanthine class of alkaloids. It is structurally similar to caffeine and shares some of its pharmacological effects. Theophylline is commonly used as a bronchodilator to treat respiratory conditions such as asthma, chronic obstructive pulmonary disease (COPD), and bronchitis. It works by relaxing the smooth muscles in the airways, making it easier to breathe. Additionally, theophylline has mild diuretic and cardiac stimulation effects, and it may also have anti-inflammatory and immunomodulatory properties. However, it also has a narrow therapeutic window, and excessive doses can lead to toxicity, with symptoms including nausea, vomiting, tremors, and accelerated heart rate.

InChI:InChI=1/C8H10N4O3/c1-11-6-5(9-4(3-13)10-6)7(14)12(2)8(11)15/h13H,3H2,1-2H3,(H,9,10)

Upstream product

• 79-14-1 glycolic Acid 
• 5440-00-6 4,5-Diamino-1,3-dimethyluracil 
• 67-56-1 methanol 
• 58-55-9 theophylline 
• 78-93-3 butanone 
• 67-64-1 acetone 
• 107-87-9 2-Pentanone 

Downstream Products

• 109437-46-9 8-(cyclohexylamino-methyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 
• 116567-96-5 1,3,1',3'-tetramethyl-3,7,3',7'-tetrahydro-8,8'-(2-cyclohexyl-2-aza-propane-1,3-diyl)-bis-purine-2,6-dione 
• 27042-48-4 7-benzyl-8-hydroxymethyl-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 
• 1802088-50-1 8-((4-(cyclopropanecarbonyl)piperazin-1-yl)methyl)-7-isopentyl-1,3-dimethyl-1H-purine-2,6(3H,7H)-dione 
• 79927-22-3 7-benzyl-1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purine-8-carbaldehyde 
• 1624255-78-2 8-(2-bromobenzyl)-1,3-dimethyl-6,7,8,9-tetrahydropyrazino[2,1-f]purine-2,4(1H,3H)-dione 
• 1624255-77-1 8-(4-fluorobenzyl)-1,3-dimethyl-6,7,8,9-tetrahydropyrazino[2,1-f]purine-2,4(1H,3H)-dione 
• 1624256-39-8 8-(3,4,5-trimethoxybenzyl)-1,3-dimethyl-6,7,8,9-tetrahydropyrazino[2,1-f]purine-2,4(1H,3H)-dione 
• 1624255-76-0 8-(3-fluorobenzyl)-1,3-dimethyl-6,7,8,9-tetrahydropyrazino[2,1-f]purine-2,4(1H,3H)-dione 

Relevant articles and documents

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Discovery of NCT-501, a Potent and Selective Theophylline-Based Inhibitor of Aldehyde Dehydrogenase 1A1 (ALDH1A1)

Aldehyde dehydrogenases (ALDHs) metabolize reactive aldehydes and possess important physiological and toxicological functions in areas such as CNS, metabolic disorders, and cancers. Increased ALDH (e.g., ALDH1A1) gene expression and catalytic activity are vital biomarkers in a number of malignancies and cancer stem cells, highlighting the need for the identification and development of small molecule ALDH inhibitors. A new series of theophylline-based analogs as potent ALDH1A1 inhibitors is described. The optimization of hits identified from a quantitative high throughput screening (qHTS) campaign led to analogs with improved potency and early ADME properties. This chemotype exhibits highly selective inhibition against ALDH1A1 over ALDH3A1, ALDH1B1, and ALDH2 isozymes as well as other dehydrogenases such as HPGD and HSD17β4. Moreover, the pharmacokinetic evaluation of selected analog 64 (NCT-501) is also highlighted.

Photochemistry of purine systems, Part III. Photoreactions of theophylline with alcohols in the presence of aliphatic ketones

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